Lactisol

Structural formula
	Simplified structural formula without stereochemistry
General
Surname	Lactisol
other names	Sodium 2- (4-methoxyphenoxy) propionate; 2- (p-Methoxyphenoxy) propionic acid, sodium salt; Na-PMP; ORP 178; Cypha; Envision; FEMA No. 3773; JECFA No. 1029;
Molecular formula	C 10 H 11 NaO 4
Brief description	colorless crystals
External identifiers / databases
EC number	604-737-4
ECHA InfoCard	100.123.510
PubChem	23670520
ChemSpider	4515110
Wikidata	Q2813794
properties
Molar mass	218.184 g mol −1
Melting point	190 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lactisol is a chemical compound from the group of phenol ethers .

properties

Lactisol occurs naturally in small amounts in roasted coffee beans , in a concentration of 0.55 to 1.2 ppm and about 80% in the ( S ) configuration [it has a center of chirality and therefore occurs in two enantiomeric forms, ( R ) and ( S )]. It inhibits the human as well gymnemic acids , Gurmarin , Hodulcine and ziziphine , the activation of the receptor for sweet taste on the tongue. The sweet taste of sugars , sugar substitutes and sweeteners is inhibited. In rats, however, it does not inhibit the sweet taste. In addition, by binding to T1R3 , it also inhibits the taste sensitivity of umami in humans . The sense of taste for salty, sour and bitter are not inhibited by lactisol.

The infrared spectrum of lactisol has been described.

use

Lactisol is used in food at a concentration between 50 and 150 ppm. In the USA in 1990 it was classified as generally recognized as safe in a concentration of up to 150 ppm . The inhibition of the sweet taste causes other aromas and tastes to come to the fore, for example the fruit aroma in jams , which generally have a high sugar content for preservation .

Individual evidence

↑ ^a ^b FAO : Sodium 2- (4-methoxyphenoxy) propanoate .
↑ ^a ^b Data sheet (±) -2- (p-Methoxyphenoxy) propionic acid, ≥98% from Sigma-Aldrich , accessed on October 4, 2018 ( PDF ).
^ Ivon Flament, Yvonne Bessière-Thomas: The individual constituents . In: Coffee flavor chemistry. John Wiley and Sons. P. 207. ISBN 0-471-72038-0 .
↑ Elner B. Rathbone, Gita D. Patel, Ronald W. Butters, Derek Cookson, Jane L. Robinson: Occurrence of 2- (4-methoxyphenoxy) propanoic acid in roasted coffee beans: analysis by gas-liquid chromatography and by high- performance liquid chromatography. In: Journal of Agricultural and Food Chemistry. 37, 1989, pp. 54ff., Doi : 10.1021 / jf00085a013 .
↑ Elner B. Rathbone, Ronald W. Butters, Derek Cookson, Jane L. Robinson: Chirality of 2- (4-methoxyphenoxy) propanoic acid in roasted coffee beans: analysis of the methyl esters by chiral high-performance liquid chromatography. In: Journal of Agricultural and Food Chemistry. 37, 1989, p. 58ff., Doi : 10.1021 / jf00085a014 .
↑ ^a ^b A. D. Kinghorn, CM Compadre: Alternative Sweeteners (Third Edition, Revised and Expanded ed.) (2001). Marcel Dekker, New York. ISBN 0-8247-0437-1 .
↑ P. Jiang, M. Cui, B. Zhao, Z. Liu, LA Snyder, LM Benard, R. Osman, RF Margolskee, M. Max: Lactisole interacts with the transmembrane domains of human T1R3 to inhibit sweet taste. In: Journal of Biological Chemistry . Volume 280, Number 15, April 2005, pp. 15238-15246, doi : 10.1074 / jbc.M414287200 , PMID 15668251 .
↑ M. Zhao, XQ Xu, XY Meng, B. Liu: The Heptahelical Domain of the Sweet Taste Receptor T1R2 Is a New Allosteric Binding Site for the Sweet Taste Modulator Amiloride That Modulates Sweet Taste in a Species-Dependent Manner. In: Journal of molecular neuroscience: MN. [Electronic publication before printing] August 2018, doi: 10.1007 / s12031-018-1156-5 , PMID 30120716 .
↑ SS Schiffman: Selective Inhibition of Sweetness by the Sodium Salt of +/- 2- (4-Methoxyphenoxy) propanoic Acid. In: Chemical Senses. 24, pp. 439-447, doi : 10.1093 / chemse / 24.4.439 .
^ A. Sclafani, C. Pérez: Cypha [propionic acid, 2- (4-methoxyphenol) salt] inhibits sweet taste in humans, but not in rats. In: Physiology & behavior. Volume 61, Number 1, January 1997, pp. 25-29, PMID 8976529 .
↑ H. Xu, L. Staszewski, H. Tang, E. Adler, M. Zoller, X. Li: Different functional roles of T1R subunits in the heteromeric taste receptors. In: Proceedings of the National Academy of Sciences . Volume 101, number 39, September 2004, pp. 14258-14263, doi: 10.1073 / pnas.0404384101 , PMID 15353592 , PMC 521102 (free full text).
↑ FAO: IR spectrum of “Sodium 2- (4-methoxyphenoxy) propanoate” .
↑ Burdock, GA, Wagner, BM, Smith, RL, Munro, IC & Newberne, PM (1990). Recent progress in the consideration of flavor ingredients under the Food Additives Amendment . 15. GRAS Substances. Food Technology, Vol. 44, pp. 78-86.
↑ Fran labell: Sugar sans sweetness - lactisole . Prepared Foods, May 1995.

[FAO-1] FAO : Sodium 2- (4-methoxyphenoxy) propanoate .

[Sigma-2] Data sheet (±) -2- (p-Methoxyphenoxy) propionic acid, ≥98% from Sigma-Aldrich , accessed on October 4, 2018 ( PDF ).

[3] Ivon Flament, Yvonne Bessière-Thomas: The individual constituents . In: Coffee flavor chemistry. John Wiley and Sons. P. 207. ISBN 0-471-72038-0 .

[Rathbone_54-4] Elner B. Rathbone, Gita D. Patel, Ronald W. Butters, Derek Cookson, Jane L. Robinson: Occurrence of 2- (4-methoxyphenoxy) propanoic acid in roasted coffee beans: analysis by gas-liquid chromatography and by high- performance liquid chromatography. In: Journal of Agricultural and Food Chemistry. 37, 1989, pp. 54ff., Doi : 10.1021 / jf00085a013 .

[Rathbone_58-5] Elner B. Rathbone, Ronald W. Butters, Derek Cookson, Jane L. Robinson: Chirality of 2- (4-methoxyphenoxy) propanoic acid in roasted coffee beans: analysis of the methyl esters by chiral high-performance liquid chromatography. In: Journal of Agricultural and Food Chemistry. 37, 1989, p. 58ff., Doi : 10.1021 / jf00085a014 .

[Kinghorn-6] A. D. Kinghorn, CM Compadre: Alternative Sweeteners (Third Edition, Revised and Expanded ed.) (2001). Marcel Dekker, New York. ISBN 0-8247-0437-1 .

[7] P. Jiang, M. Cui, B. Zhao, Z. Liu, LA Snyder, LM Benard, R. Osman, RF Margolskee, M. Max: Lactisole interacts with the transmembrane domains of human T1R3 to inhibit sweet taste. In: Journal of Biological Chemistry . Volume 280, Number 15, April 2005, pp. 15238-15246, doi : 10.1074 / jbc.M414287200 , PMID 15668251 .

[8] M. Zhao, XQ Xu, XY Meng, B. Liu: The Heptahelical Domain of the Sweet Taste Receptor T1R2 Is a New Allosteric Binding Site for the Sweet Taste Modulator Amiloride That Modulates Sweet Taste in a Species-Dependent Manner. In: Journal of molecular neuroscience: MN. [Electronic publication before printing] August 2018, doi: 10.1007 / s12031-018-1156-5 , PMID 30120716 .

[Schiffman-9] SS Schiffman: Selective Inhibition of Sweetness by the Sodium Salt of +/- 2- (4-Methoxyphenoxy) propanoic Acid. In: Chemical Senses. 24, pp. 439-447, doi : 10.1093 / chemse / 24.4.439 .

[10] A. Sclafani, C. Pérez: Cypha [propionic acid, 2- (4-methoxyphenol) salt] inhibits sweet taste in humans, but not in rats. In: Physiology & behavior. Volume 61, Number 1, January 1997, pp. 25-29, PMID 8976529 .

[11] H. Xu, L. Staszewski, H. Tang, E. Adler, M. Zoller, X. Li: Different functional roles of T1R subunits in the heteromeric taste receptors. In: Proceedings of the National Academy of Sciences . Volume 101, number 39, September 2004, pp. 14258-14263, doi: 10.1073 / pnas.0404384101 , PMID 15353592 , PMC 521102 (free full text).

[12] FAO: IR spectrum of “Sodium 2- (4-methoxyphenoxy) propanoate” .

[13] Burdock, GA, Wagner, BM, Smith, RL, Munro, IC & Newberne, PM (1990). Recent progress in the consideration of flavor ingredients under the Food Additives Amendment . 15. GRAS Substances. Food Technology, Vol. 44, pp. 78-86.

[14] Fran labell: Sugar sans sweetness - lactisole . Prepared Foods, May 1995.